Walking Safely in High Heels while Crossdressing

For many new crossdressers, walking safely in high heels while crossdressing is one of the most important goals to meet. It can also be one of the more challenging. This guide for new crossdressers will help you succeed at that goal.

A Step-by-Step Guide to Learning to Walk in High Heels

I highly recommend that one gradually learns walking safely in high heels while crossdressing. My suggested approach has three key principles:

  • To increase stability, gradually increase the height of the heels.
  • For increasing strength, slowly increase the length of time wearing heels.
  • To increase safety, master easier walking surfaces before those that are more challenging.

This article focuses on the third principle, mastering increasingly difficult walking surfaces. I explain the other principles for learning to walk in high heels in other articles.

3rd Key Tenet:
Walking Safely in High Heels while Crossdressing

In earlier posts, I discussed the 1st key tenet: Stability. This is making sure you can handle what is under your foot, namely your shoe. The 2nd key tenet to successfully wearing high heels is to develop strength. This is your foot itself, not the shoe. The 3rd and last tenet is walking safely in high heels while crossdressing, doing so on various surfaces. This is what is under your shoe.

Walking in high heels is a lot different from walking, say, in athletic shoes. With a good pair of sneakers, one is able to navigate on almost any surface, except perhaps ice. One can also learn to walk on most surfaces with high heels, but one must do it with intentional thought.

Safety can become a major problem when walking in high heels. The National Safety Council wrote a report on the types of high heel injuries.

Taking Baby Stepswalking safely in high heels while crossdressing baby steps

Think of how a baby learns how to walk. As an example, a new toddler may have to pull herself up using a coffee table, and then cruise along that coffee table while taking steps. She falls down often, then gets up and tries again.

Compare that to a high school athlete, who is able to run up and down the field without thinking. Sure, the athlete may take a fall from time to time, but largely it as easy as riding a bicycle once learned.

With the new toddler, some surfaces are easier to learn to walk upon than others. In addition, some of those surfaces are more gentle to fall upon. Landing on a nice carpeted floor is much nicer than falling on gravel, right?

For walking safely in high heels while crossdressing, first focus on surfaces that are easier and safer. Once you have mastered those surfaces, you can move on to other surfaces that are more challenging.

Crossdresser High Heels on Carpet

Carpet is King

In my opinion, a short-length carpet is ideal for walking safely in high heels while crossdressing. This is because it causes a good amount of friction while you are walking. However, be careful not to start on long-length carpets such as shag. With the longer lengths of shag carpeting, it is possible for your heel to snag.

Other indoor surfaces, such as wood, tile, and concrete, don’t offer as much friction. Although this isn’t so much a problem when the ball of your foot is on the ground, it does cause some issues with sliding when the heel hits the surface.

When you think of how you walk in your daily shoes, when your foot first hits the ground, it is the heel that strikes the surface first. This is quite easy when your heel has a large surface area. With narrow high heels, such as stilettos, it is a very small surface area that strikes the surface. This provides a smaller area with which to get suitable friction.

Think of your narrow heel as being somewhat like a pencil tip. Imagine placing the tip on the carpet, then trying to move the tip across the carpet. It would be difficult to do. Now imagine it on a smooth surface such as wood, tile, or concrete. Pushing the tip is now very easy. This is the same principle for how the carpet keeps your heel from slipping out from under you as you walk.

Walking on Smooth Surfaces

Once you become very comfortable walking on carpet, you can try smoother surfaces. I feel that one is in good shape to go ahead once she can do a little running on the carpet without falling. I’m not talking about sprinting across a room. Simply being able to start a jog for a couple of steps, then stopping abruptly, is a good test of mastery on the carpet.

For walking safely in high heels while crossdressing, I think the key to success on smooth surfaces is to develop the mindset of intentionally setting your heel firmly upon the surface. Most of my near falls on tile were due to the heel barely striking the surface before putting my weight on it. So a good technique for doing better is to walk in a horse trot, where your both the ball of your foot and your heel strike the surface at the same time. Believe me, it will look quite ridiculous, but this is what it takes to get better.

You should do this horse trot until you can do it without thinking. Once you have mastered it over several sessions, start walking with your heel coming down just a little before the ball. When you do this, your heel is coming down somewhat hard and straight, like when doing the horse trot, but it is only the heel that is coming down first. This is how you learn about becoming very deliberate about setting your heel down firmly, with you pushing your foot down and not just setting it down.

Using a Smaller Stride

One thing you’ll notice with this technique is that your stride will be smaller than what you have when walking in flats, such as athletic shoes. What you’ll want for walking safely in high heels while crossdressing is for the ball of your foot to come down almost immediately after your heel strikes the floor. This requires you to take shorter, daintier steps. In fact, this is good news in that you’ll want to learn to take daintier steps while walking in heels anyway.

What this does, over time, is to help develop the habit of getting your weight off your heel as quickly as possible. Doing this maximizes the amount of friction your small heel has on the smooth surface. This is the key skill, and one has mastered it, you are free to start walking in your normal way. Of course, you will continue to take shorter steps because of the need for the ball of your foot to come down very shortly after the heel.

Learning to walk outside

Outdoor Surfaces

Compared to indoor surfaces, the outdoors presents a number of new challenges for walking safely in high heels while crossdressing. These include:

  • Uneven surfaces, such as cracks in a sidewalk
  • Unstable surfaces, including gravel walkways
  • Soft surfaces, such as well-watered lawns
  • Additional hazards, including sticks or drainage grates

Your primary concern is to avoid twisting your ankle or falling. The best thing you can do is being observant. When possible, you’ll want to seek places where you heel will land on the most stable surface available. For example, when walking down a sidewalk, look far enough ahead that you can plan for your heel to avoid the cracks.

When I was a child, I played a game where I didn’t step on cracks. The saying was something like “Step on a crack, break your mother’s back.” When wearing heels, you can change the game to try to have the ball of your foot nearly always land on the crack. If the ball is on the crack, then your heel isn’t on the crack, right?

Of course, you don’t have to have the ball of your foot always land on the cracks. Just avoid having your heel land on them. However, making a game of this at first may help you become more aware of the hazard. After all, you didn’t have to worry about it when you wore only athletic shoes. Now you have to worry.

Walking in heels on the lawnWalking on Lawns

The trick to walking on lawns is to remember that if the ground is soft enough, your heels will sink. The first time I tried it, I didn’t know it was going to happen. Needless to say, I was quite surprised when that first step almost knocked me to the ground!

On the grass, the key to walking safely in high heels while crossdressing is to put most of your weight upon the balls of your feel. This will not feel natural, nor will it feel good trying to tippy toe your way across a lawn. It sure beats falling on your bottom though!

For the most part, my advice is to avoid grass when walking in heels. If your plan is being on a lawn for an extended period, I suggest using either flats, wedges, or heels that are wide enough not to penetrate the ground. Stilettos are not a good substitute for a core aerator when it comes to lawn care.

Up the Down Staircase

One of the things that took me a while to figure how to do was walking up and down steep staircases. At first, I tried walking with my shoes at an angle, so that the entire shoe was on the step. I found a couple of problems with this. First, it made me look like an idiot. Second, sometimes my foot wasn’t angled enough, causing the heel to slip off the step.

Going Downstairs at an Angle
Going Upstairs at an Angle

After a month or so, I finally figured out how to do it better! I discovered I didn’t need to angle my feet to walk up and down the stairs safely.

Walking Upstairs with Heel Off Step

The trick for going up the stairs is to have the heel miss the step. This makes only the ball of your foot land on the step. This gives great support.

In the picture, I am exaggerating how far down the heel is going down when stepping up. It was a difficult shot for me to take so that it is obvious the heel is not on the step. In reality, the heel isn’t that far down. Furthermore, if you are walking up steps that have more room, you can feel free to have your entire foot, including the heel, fully on each step. Be sure when you are doing this that your heel is consistently away from the edge. You don’t want to surprise yourself by tumbling down the staircase. There is no way for a woman to look graceful while spilling down the stairs!

Down the Up Staircase

Going Downstairs with Heel Back

For going down the stairs, I just made a habit of putting my heel all the way back. The toe will extend over the edge of the step, but there is plenty of support. For a while, I overexaggerated by pushing my heel against the upper step. Over time I have gotten to where there is a narrow gap between the heel and the upper step.

Ball of Foot Missing the Step

When going down a stairway, be sure the ball of your foot doesn’t extend too far past the edge. You don’t want to go tumbling down (like I almost did when taking this picture).

Walking Safely

As a crossdresser, learning how to walk in high heels by practicing the three tenets (stability, strength, and safety) is your key to success. Thank you for taking the time to read these articles and good luck to you on your crossdressing journey!

xoxoxo Sami


How did you learn to walk in high heels? Leave a comment

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Posted by Sami

Sami has been a part-time crossdresser for about 5 years. Although she still has a lot to learn herself, she is enjoying teaching new crossdressers tips that will hopefully help them on their adventure.

Besides enjoying her time with her family and working as a web developer, Sami loves to travel, make home improvements, and create jewelry in her spare time.

Read more about Sami by clicking her name.

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